All substantive areas of law, with no exception, have a common concern for the processes by which legal disputes get resolved. Naturally, the success of any particular litigation strategy in a legal dispute depends on several factors, such as procedural costs, the judges' accuracy and, most importantly, the litigation strategy followed by the counterpart. Previous work within the legal scholarship has focused on the outcomes of the litigation process and their concordance with the merits of the claims presented by the parties. In contrast, in this paper, we adopt a dynamic view of the legal system as a whole. In order to do this, we propose an evolutionary point of view. That is, we assume that the most successful litigation strategies at a certain time are more likely to be followed in the future, so the prevalence of different strategies in the system will generally change over time. Importantly, this change in the frequency of litigation strategies in the legal system will, in turn, affect the relative success of each litigation strategy, thus creating a double feedback loop between prevalence and success of litigation strategies, which we aim to explore. Furthermore, we will compare the results drawn from our model with the ones proposed by the empirical literature on the topic. Thus, the main purpose of this paper is to offer a novel approach to study legal disputes, looking at the whole litigation system as a single entity that evolves through time. In particular, we focus on cases of medical liability, and use agent-based simulation to provide a dynamic view of how various factors affect the type of litigation strategies that are successful and prevail in a certain judicial context.